Diamide

Base Information

• Chemical Name: Diamide
• CAS No.: 10465-78-8
• Molecular Formula: C6H12N4O2
• Molecular Weight: 172.187
• Hs Code.: 29270000
• European Community (EC) Number: 233-951-7
• NSC Number: 143013
• UNII: 86EQC90W32
• Wikipedia: Tetramethylazodicarboxamide
• ChEMBL ID: CHEMBL1255835
• Mol file: 10465-78-8.mol

Synonyms:Acid Bisdimethylamide, Diazodicarboxylic;Bisdimethylamide, Diazodicarboxylic Acid;Diamide;Diazodicarboxylic Acid Bis(N,N-dimethyl)amide;Diazodicarboxylic Acid Bisdimethylamide;Dizene Dicarboxylic Acid Bis(N,N-dimethylamide);Dizenedicarboxylic Acid Bis(N,N-dimethylamide);Tetramethylazoformamide

Chemical Property of Diamide

Chemical Property:

• Appearance/Colour: bright yellow solid
• Melting Point: 112 °C
• Boiling Point: 220.4 °C at 760 mmHg
• PKA: -0?+-.0.70(Predicted)
• Flash Point: 87.1 °C
• PSA: 65.34000
• Density: 1.13 g/cm³
• LogP: 0.80180
• Storage Temp.: −20°C
• Solubility.: soluble in Methanol
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 172.09602564
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

98% ^*data from raw suppliers

1,1'-Azobis(N,N-dimethylformamide) >97.0%(T) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CN(C)C(=O)N=NC(=O)N(C)C
• Isomeric SMILES: CN(C)C(=O)/N=N/C(=O)N(C)C
• Description: N,N,N’,N’-Tetramethylazodicarboxamide (also named as Diamide, TMAD) is a reagent used for the oxidization of thiols in proteins. It is used as a reagent in the Mitsunobu reaction in place of diethyl azodicarboxylate. It can be used to titrate protein gluotathiolation to discriminate from other protein modifications.
• Uses: Reported to be of use as a thiol oxidizing agent. Diamide has been used to titrate protein glutathiolation to discriminate from other oxidative protein modifications. Treatment increased protein glutathiolation in a concentration-dependent manner and had comparably little effect on protein-protein disulfide formation.

Technology Process of Diamide

There total 5 articles about Diamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

1,2-bis(N,N-dimethylcarbamoyl)hydrazine (17696-89-8) → diamide (10465-78-8)

Guidance literature:

With pyridine; N-Bromosuccinimide; Ambient temperature;

DOI:10.1246/cl.1994.539

Reference yield:

dimethyl amine (124-40-3) + diethylazodicarboxylate (1972-28-7,218603-74-8) → diamide (10465-78-8)

Guidance literature:

In methanol; diethyl ether;

Reference yield:

→ diamide (10465-78-8)

Guidance literature:

Diaethylazodicarboxylat, (CH3)2NH;

DOI:10.1021/jo00949a007

upstream raw materials:

1,2-bis(N,N-dimethylcarbamoyl)hydrazine

dimethyl amine

diethylazodicarboxylate

Downstream raw materials:

C₁₃H₂₀N₄O₄S

4-(4-formylphenoxy)piperidine-1-carboxylic acid t-butyl ester

(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(2-thenyloxy)-1H-1,4-benzodiazepine

2-[3-(4-Morpholinyl)phenoxy]ethyl 3-(1-piperazinyl)-2-pyrazinyl Ether

Refernces

• 1、 Kraebel,Davis. "". . p. 2226. Retrieved 1969.
• 2、 Smissman,Mahriyannis. "-". . p. 1652,1655. Retrieved 1973.
• 3、 Tsunoda, Tetsuto,Otsuka, Junko,Yamamiya, Yoshiko,Ito, Sho. "N,N,N',N'-Tetramethylazodicarboxamide (TMAD), A New Versatile Reagent for Mitsunobu Reaction. Its Application to Synthesis of Secondary Amines". . p. 539 - 542. Retrieved 2007/10/02.